2-hydroxy-1-naphthaldehyde nicotinoyl hydrazone | 15017-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-1-naphthaldehyde nicotinoyl hydrazone
• 英文别名: 2-hydroxy-1-naphthaldehyde nicotinoylhydrazone；2-hydroxynaphthaldehyde nicotinoylhydrazone；2-hydroxynaphthaldehyde pyridinoylhydrazone；Hydroxynaphthaldehyde nicotinoylhydrazone；N-[(2-hydroxynaphthalen-1-yl)methylideneamino]pyridine-3-carboxamide
• CAS: 15017-29-5
• 化学式: C₁₇H₁₃N₃O₂
• mdl: MFCD00406292
• 分子量: 291.309
• InChiKey: UEHLSZJDQXWTDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-1-naphthaldehyde nicotinoyl hydrazone 以 甲醇 、 水 为溶剂， 反应 0.17h， 生成 [Ge(Nnf)₂]
  参考文献：
  名称：

  Ge（IV）四氯化钴（2-羟基芳醛）吡啶基（氨基苯甲酰基）的配合物的合成，光谱，磁性和热性质

  摘要：

  2-羟基苯并（2-羟基-1-萘）醛（H 2 L）-CoCl 2-甲醇系统的GeCl 4-烟酰基（异烟酰基，2-或4-氨基苯甲酰基）中的相互作用导致形成锗的螯合物[Ge（L·H）2 ] 2+在外螯合氮原子（N Py或NH 2）上质子化的[Ge（L·H）2 ] [CoCl 4 ]· n CH 3 OH配合物阳离子。揭示了电解离解的类型和配合物的热解特性。已经研究了配合物的光谱，热和磁性质。

  DOI：

  10.1134/s1070363217010170
• 作为产物：
  描述：

  烟酸乙酯 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 13.5h， 生成 2-hydroxy-1-naphthaldehyde nicotinoyl hydrazone
  参考文献：
  名称：

  一类用于治疗心力衰竭的酰腙类衍生物

  摘要：

  本发明属于医药技术领域，涉及如下通式I所示的一类酰腙类衍生物的设计及制备方法，可用于治疗包括充血性心力衰竭的收缩性心力衰竭。

  公开号：

  CN105481765A

文献信息

• Tin(IV) complexes with 2-hydroxybenz(2-hydroxynaphth)aldehyde nicotinoylhydrazones (H2Ns, H2Nnf). Molecular and crystal structures of [SnCl3(HNnf)] · 2DMF
  作者：N. V. Shmatkova、I. I. Seifullina、Z. A. Starikova

  DOI：10.1134/s1070328415050073

  日期：2015.5

  The reaction of SnCl4 with 2-hydroxybenz(2-hydroxynaphth)aldehyde nicotinoylhydrazones (H2Ns, H2Nnf) in CH3OH gave non-electrolyte complexes [SnCl3(HNs)] (I) and [SnCl3(HNnf)] (II), which were recrystallized to give the solvates [SnCl3(HNs)] · DMF (III) and [SnCl3(HNnf)] · 2DMF (IV). It was found by IR spectroscopy that the ligands in I–IV are protonated at the N(Py) and coordinated in the tridentate

  SnCl 4与2-羟基苯并（2-羟基萘）醛烟酰肼（H 2 Ns，H 2 Nnf）在CH 3 OH中的反应产生了非电解质络合物[SnCl 3（HNs）]（I）和[SnCl 3（HNnf） ）]（II），将其重结晶，得到溶剂化物[SnCl 3（HNs）]·DMF（III）和[SnCl 3（HNnf）]·2DMF（IV）。通过红外光谱发现，I – IV中的配体它们在N（Py）上质子化，并通过偶氮甲碱氮原子以及氧和氧嗪氧原子以三齿螯合模式配位。I – IV的热解以及电子撞击引起的I和II的断裂伴随有络合物[SnCl 2（Ns）]和[SnCl 2（Nnf）]的形成。IV的分子和晶体结构通过X射线衍射测定（CIF文件CCDC号816105）。
• Narang, Rakesh; Narasimhan, Balasubramanian; Sharma, Sunil, Letters in drug design and discovery, 2011, vol. 8, # 9, p. 733 - 749
  作者：Narang, Rakesh、Narasimhan, Balasubramanian、Sharma, Sunil、Sriram, Dharmarajan、Yogeeswari, Perumal、De Clercq, Erik、Pannecouque, Christophe、Balzarini, Jan

  DOI：——

  日期：——
• Novel multifunctional iron chelators of the aroyl nicotinoyl hydrazone class that markedly enhance cellular NAD ⁺ /NADH ratios
  作者：Zhixuan Wu、Duraippandi Palanimuthu、Nady Braidy、Nor Hawani Salikin、Suhelen Egan、Michael L.H. Huang、Des R. Richardson

  DOI：10.1111/bph.14963

  日期：2020.5

  Background and PurposeAlzheimer's disease (AD) is a multifactorial condition leading to cognitive decline and represents a major global health challenge in ageing populations. The lack of effective AD therapeutics led us to develop multifunctional nicotinoyl hydrazones to target several pathological characteristics of AD.Experimental ApproachWe synthesised 20 novel multifunctional agents based on the nicotinoyl hydrazone scaffold, which acts as a metal chelator and a lipophilic delivery vehicle, donating a NAD+ precursor to cells, to target metal dyshomeostasis, oxidative stress, β‐amyloid (Aβ) aggregation, and a decrease in the NAD+/NADH ratio.Key ResultsThe most promising compound, 6‐methoxysalicylaldehyde nicotinoyl hydrazone (SNH6), demonstrated low cytotoxicity, potent iron (Fe)‐chelation efficacy, significant inhibition of copper‐mediated Aβ aggregation, oxidative stress alleviation, effective donation of NAD+ to NAD‐dependent metabolic processes (PARP and sirtuin activity) and enhanced cellular NAD+/NADH ratios, as well as significantly increased median Caenorhabditis elegans lifespan (to 1.46‐fold of the control); partly decreased BACE1 expression, resulting in significantly lower soluble amyloid precursor protein‐β (sAPPβ) and Aβ1–40 levels; and favourable blood–brain barrier‐permeation properties. Structure–activity relationships demonstrated that the ability of these nicotinoyl hydrazones to increase NAD+ was dependent on the electron‐withdrawing or electron‐donating substituents on the aldehyde‐ or ketone‐derived moiety. Aldehyde‐derived hydrazones containing the ONO donor set and electron‐donating groups were required for NAD+ donation and low cytotoxicity.Conclusions and ImplicationsThe nicotinoyl hydrazones, particularly SNH6, have the potential to act as multifunctional therapeutic agents and delivery vehicles for NAD+ precursors for AD treatment.
• Germanium(IV) bischelates with 2-hydroxynaphthaldehyde pyridinoylhydrazones: The crystal and molecular structure of the complex with isonicotinoylhydrazone (H2Inf), [Ge(Inf · HCl)2] · 5H2O
  作者：I. I. Seifullina、N. V. Shmatkova、O. V. Shishkin、R. I. Zubatyuk

  DOI：10.1134/s0036023607040043

  日期：2007.4

  The reactions of GeCl4 with 2-hydroxynaphthaldehyde pyridinoylhydrazones (H2L) in methanol give complexes [Ge(L center dot HCl)(2)] center dot nH(2)O. The data of mass spectrometry, thermogravimetry, and IR and H-1 NMR spectroscopy indicate that the ligand molecules are protonated at the pyridine nitrogen atom with hydrogen chloride and coordinated to germanium in the tridentate mode through the azomethine nitrogen atom and the oxyazine and oxy group oxygen atoms. The structure of the complex with isonicotinoylhydrazone (H(2)Inf), [Ge(Inf center dot HCl)(2)] center dot 5H(2)O has been determined by X-ray diffraction.